Book Holiday Homes in Oakland

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Featured Holiday Homes in Oakland

Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting

Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting

Mount Vernon
Stay at this vacation home in Mount Vernon. Enjoy an in-room coffeemaker and in-room fireplaces. Popular attractions Lake Minnehonk and Town Beach are located ...
Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting
Private and Calming Waterfront to the Rescue!

Private and Calming Waterfront to the Rescue!

Augusta
Stay at this vacation home in Augusta. Enjoy free WiFi, patios, and cable/satellite TV service. Popular attractions Viles Arboretum and Pine Tree State Arboretum ...
Private and Calming Waterfront to the Rescue!
Beautiful lakeside 4 bedroom retreat with private dock and walkout basement

Beautiful lakeside 4 bedroom retreat with private dock and walkout basement

2 out of 5
Oakland
Book a stay at this family-friendly vacation home in Oakland. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Tree Spirits and Belgrade ...
Beautiful lakeside 4 bedroom retreat with private dock and walkout basement
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Spectacular Cobbossee Lakefront with Hot Tub&Dog Friendly

Spectacular Cobbossee Lakefront with Hot Tub&Dog Friendly

Manchester
Book a stay at this golf vacation home in Manchester. Enjoy free WiFi, a garden, and tennis courts. Popular attractions Cobbosseecontee Lake and Augusta Country ...
Spectacular Cobbossee Lakefront with Hot Tub&Dog Friendly
The Modern Maine Retreat

The Modern Maine Retreat

Oakland
Stay at this vacation home in Oakland. Enjoy free WiFi, an in-room coffeemaker, and air conditioning. Popular attractions Tree Spirits and First Congregational ...
The Modern Maine Retreat
Brand New Waterfront Lake House (completed July 2021)

Brand New Waterfront Lake House (completed July 2021)

Belgrade
Stay at this vacation home in Belgrade. Enjoy free WiFi, a garden, and patios. Popular attractions Belgrade Lakes Chain and Belgrade Lakes Golf are located ...
Brand New Waterfront Lake House (completed July 2021)
Peaceful Fisherman's Paradise w/ Deck + Fire Pit!

Peaceful Fisherman's Paradise w/ Deck + Fire Pit!

Winthrop
Book a stay at this beach vacation home in Winthrop. Enjoy a beach locale, patios, and an in-room coffeemaker. Popular attractions Annabessacook Lake and Wilson ...
Peaceful Fisherman's Paradise w/ Deck + Fire Pit!
Cozy House in the heart of Waterville Maine.

Cozy House in the heart of Waterville Maine.

Waterville
Stay at this vacation home in Waterville. Enjoy a garden, an in-room coffeemaker, and air conditioning. Popular attractions Redington Museum and Common Street ...
Cozy House in the heart of Waterville Maine.
Spectacular Location  Reasonably Priced

Spectacular Location Reasonably Priced

Belgrade
Stay at this vacation home in Belgrade. Enjoy patios, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Belgrade Lakes Golf and Belgrade ...
Spectacular Location Reasonably Priced
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Oakland Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Oakland vacation homes are the perfect way for you to wing it.

Holiday houses in Oakland let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Oakland in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Oakland adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Oakland with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Oakland vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Oakland Holiday Homes essential information

Accommodation
139 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting, Private and Calming Waterfront to the Rescue!, Beautiful lakeside 4 bedroom retreat with private dock and walkout basement, Spectacular Cobbossee Lakefront with Hot Tub&Dog Friendly, The Modern Maine Retreat, Brand New Waterfront Lake House (completed July 2021), Peaceful Fisherman's Paradise w/ Deck + Fire Pit!, Cozy House in the heart of Waterville Maine., Spectacular Location Reasonably Priced

Top trending hotels in Oakland

Cozy Long Pond Cottage: private mooring & shared dock

Cozy Long Pond Cottage: private mooring & shared dock

Rome
Book a stay at this family-friendly vacation home in Oakland. Enjoy free WiFi, a water park, and an in-room coffeemaker. Popular attractions Belgrade Lakes Golf ...
Cozy Long Pond Cottage: private mooring & shared dock
Weekly discounts avail. Get away from it all on the start of  The Belgrade Lakes

Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes

Oakland
Stay at this cottage in Oakland. Enjoy free WiFi, patios, and cable/satellite TV service. Popular attraction Tree Spirits is located nearby.
Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes
Belgrade Lakes Cottage w/ Long Pond beach access close to Augusta, Colby College

Belgrade Lakes Cottage w/ Long Pond beach access close to Augusta, Colby College

Rome
Stay at this cottage in Oakland. Enjoy a garden, patios, and air conditioning. Popular attractions Belgrade Lakes Golf and Belgrade Lakes Chain are located ...
Belgrade Lakes Cottage w/ Long Pond beach access close to Augusta, Colby College
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Lakefront Maine House ~ 4 Mi to Colby College

Lakefront Maine House ~ 4 Mi to Colby College

Oakland
Stay at this vacation home in Oakland. Enjoy patios, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Tree Spirits and Redington Museum ...
Lakefront Maine House ~ 4 Mi to Colby College
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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^Subject to availability and chosen travel dates.